US5668204A - Stabilization of polycarbonates having high heat distortion temperatures - Google Patents

Stabilization of polycarbonates having high heat distortion temperatures Download PDF

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Publication number
US5668204A
US5668204A US07/853,670 US85367092A US5668204A US 5668204 A US5668204 A US 5668204A US 85367092 A US85367092 A US 85367092A US 5668204 A US5668204 A US 5668204A
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alkyl
denote
denotes
aryl
integer
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Helmut-Martin Meier
Uwe Westeppe
Rolf Dhein
Dieter Freitag
Dieter Constant
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Bayer AG
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Bayer AG
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Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: WESTEPPE, UWE, CONSTANT, DIETER, FREITAG, DIETER, DHEIN, ROLF, MEIER, HELMUT-MARTIN
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/549—Silicon-containing compounds containing silicon in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Definitions

  • the invention concerns thermoplastic polycarbonate molding compositions and more particularly to compositions having an improved impact performance.
  • thermoplastic molding composition containing an aromatic polycarbonate and a particular siloxane compound is disclosed.
  • the composition which is based on a polycarbonate resin having bifunctional structural units corresponding to formula (Ia) ##STR4## wherein R 1 and R 2 denote, independently of one another, hydrogen, halogen, C 1 -C 8 alkyl, C 5 -C 6 -cycloalkyl, C 6 -C 10 -aryl, or C 7 -C 12 -aralkyl,
  • n 1 or 2
  • R 3 and R 4 selected individually for each X denote, independently of one another, hydrogen or C 1 -C 6 -alkyl
  • R 3 and R 4 are both alkyl groups on at least one X atom
  • u denotes an integer from 1 to 20
  • v and w denote an integer from 0 to 20
  • A denotes a C 1 -C 20 -alkyl group or a C 6 -C 10 -aryl group is characterized in its improved heat distortion temperature and good aging properties.
  • Monomeric siloxanes in conventional polycarbonates are disclosed in DOS 2,920,450. Oligomeric siloxanes in conventional polycarbonates are disclosed in DOS 2,832,342. Cyclic siloxanes in conventional polycarbonates are disclosed in DOS 2,832,339. Vinyl polymers containing silicon epoxide in filled conventional polycarbonates are disclosed in DOS 2,327,014 (LeA 15 025). No improvement in impact strength in the course of long term aging is observed in these products. Glass fiber reinforced polycarbonates with improved mechanical properties obtained by the addition of organopolysiloxanes are disclosed in DE-OS 2 518 287 (Le A 16 254) Polycarbonates corresponding to structural formulae (Ia) are not mentioned there.
  • DE-OS 2,920,451 (Le A 19 567) discloses the use of organic silicon compounds in combination with oxetane compounds, dioxanes or tetrahydrofurans for the stabilization and brightening of polycarbonates.
  • Polycarbonates corresponding to structural formulae (Ia) are again not mentioned there.
  • the aromatic polycarbonates of the present invention have high heat distortion temperatures and weight average molecular weights (Mw) of at least 10,000, preferably from 10,000 to 200,000 and in particular from 20,000 to 80,000, and are characterized in having bifunctional carbonate structural units corresponding to formula (Ia) ##STR7## wherein R 1 and R 2 denote, independently of one another, hydrogen, halogen, preferably chlorine or bromine, C 1 -C 8 alkyl, C 5 -C 6 -cycloalkyl, C 6 -C 10 -aryl, preferably phenyl, or C 7 -C 12 -aralkyl, preferably phenyl-C 1 -C 4 -alkyl, in particular benzyl,
  • n stands for an integer from 4 to 7, preferably 4 or 5
  • the R 3 's and R 4 's, which are selected individually for each X denote, independently of one another, hydrogen or C 1 -C 6 -alkyl
  • R 3 and R 4 are both alkyl groups on at least one X atom.
  • the polycarbonates based on the carbonate structural units of formula (Ia) are known from DE-OS 3,832,396. They are homopolycarbonates or copolycarbonates containing the structures corresponding to formula (Ia) in quantities of from 100 mol-% to 2 mol-%, preferably from 100 mol-% to 5 mol-%, in particular from 100 mol-% to 10 mol-%, most preferably from 100 mol-% to 20 mol-% in the polycarbonate, based in each case on the total 100 mol-% of difunctional carbonate structural units.
  • R 3 and R 4 are preferably both alkyl on one or two X atoms, in particular on only one X atom.
  • the preferred alkyl group is methyl.
  • the X atoms in the ⁇ -position to the diphenyl substituted carbon atom (C-1) are preferably not dialkyl substituted but alkyl disubstitution is preferred in the ⁇ -position to C-1.
  • Structural units corresponding to formula (Ia) may in particular be dihydroxydiphenyl cycloalkane groups having 5 or 6 ring carbon atoms in the cycloaliphatic residue, such as ##STR8##
  • These polycarbonates thus contain other difunctional carbonate structural units in the quantity required to make up the 100 mol-%, for example, carbonate structural units corresponding to formula (Ib) ##STR9## wherein Z denotes an aromatic group having 6-30 carbon atoms, in other words, in quantities of from 0 mol-% (inclusive) to 98 mol-% (inclusive), preferably from 0 mol-% to 95 mol-% and in particular from 0 mol-% to 90 mol-%, most preferably from 0 mol-% to 80 mol-%, based in each case on the total 100 mol-% of difunctional carbonate structural units in the polycarbonate.
  • Preferred polycarbonates include those in which the structural units corresponding to formula (Ia) correspond to formula (Ic) ##STR10## wherein R 1 and R 2 have the meanings indicated for formula (Ia), but hydrogen is particularly preferred.
  • composition of the invention contains from 0.001 to 1% by weight, preferably from 0.01 to 0.5% by weight, of at least one siloxane corresponding to formula (II) ##STR11## wherein R denotes hydrogen, C 1 -C 20 -alkyl, C 6 -C 10 -aryl or C 1 -C 10 -alkoxy,
  • r stands for zero or an integer from 1 to 200
  • s stands for zero or an integer from 1 to 200 and
  • u stands for an integer from 1 to 20,
  • v stands for zero or an integer from 1 to 20
  • w stands for zero or an integer from 1 to 20 and u+v+w ⁇ 3, and
  • A denotes a C 1 -C 20 -alkyl group or a C 6 -C 10 -aryl group optionally containing hetero atoms or epoxy or oxetane groups,
  • the present invention also relates to the use of the siloxanes corresponding to formulae (II) and/or (III) as impact strength modifiers for polycarbonates with high heat distortion temperatures based on the structural units corresponding to formula (Ia).
  • siloxanes corresponding to formulae (II) and (III) may be used singly or as mixtures of siloxanes of the same formula or mixtures of siloxanes of both formula (II) and formula (III).
  • siloxanes corresponding to formula (II) include polysiloxanes having the following parameters:
  • R hydrogen, methyl, ethyl, propyl, butyl, octyl, isooctyl, 2-ethylhexyl, phenyl or naphthyl,
  • siloxanes corresponding to formula (II) are those in which
  • R CH 3 or C 6 H 5 ,
  • Suitable siloxanes corresponding to formula (III) include cyclic siloxanes having the following parameters:
  • R methyl, ethyl, propyl, butyl, octyl, isooctyl, 2-ethylhexyl, phenyl or naphthyl,
  • the molding compositions of the invention exhibit improved resistance to aging effects including a higher retention of optical properties and impact performance.
  • siloxanes corresponding to formulae (II) and (III) in the polycarbonates is carried out in kneaders or extruders.
  • the siloxanes may in many cases be added to the above-mentioned polycarbonates during their preparation or to the starting materials.
  • the siloxanes may also be added to the solutions of the above-mentioned polycarbonates and the solvents may then be evaporated off.
  • the present invention thus also relates to a process for the preparation of the polycarbonates according to the invention, characterized in that the siloxanes corresponding to formulae (II) and (III) are incorporated in the polycarbonates by means of kneaders or extrudes or added to the starting materials during the preparation of the polycarbonates or added to solutions of the polycarbonates, followed by evaporation of the solvent, oxetanes and/or epoxides being optionally incorporated at the same time.
  • the polycarbonates may be mixed with the usual additives during or after their preparation.
  • additives include Mold release agents, dyes, inorganic pigments, [IV absorbents, flame retardants, stabilizers, fillers such as glass fibers, graphite, metal powders, etc.
  • polycarbonate molding compositions according to the invention may be used as molded products wherever known polycarbonates have hitherto been used, i.e. in the electrical industry and in the building industry for coverings and glazings, especially when high dimensional stability under heat is required in combination with good processing properties, in other words for the production of complicated parts having high heat distortion temperatures.
  • the product investigated was a copolycarbonate based on 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and 2,2-(4-hydroxyphenyl)-propane in a molar ratio of 36:65 having a relative solution viscosity of 1.295 (determined in methylene Chloride at 25° C. and at a concentration of 0.5 gm/100 ml).
  • the transmission was determined according to ASTM 1003, the yellowness index according to ASTM D 1925 and the impact strength according to DIN 53 453.
  • copolycarbonate contained, as additive,
  • copolycarbonate contained as additive 0.03% by weight of the siloxane of the following formula ##STR21##
  • This siloxane is prepared from the corresponding methyl hydrogen polysiloxane by reaction with allyl glycidyl ether according to DAS 1,272,550.
  • the incorporation in the copolycarbonate is carried out in the extruder.
  • a standard small bar was produced from the additive-containing copolycarbonate.
  • copolycarbonate contained as additive 0.03% by weight of the siloxane according to Test D and 0.3% by weight of an UV stabilizer of the formula ##STR22##
  • the incorporation of the additives in the copolycarbonate is carried out in the extruder.
  • a standard small bar was produced from the additive-containing copolycarbonate.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US07/853,670 1991-03-26 1992-03-19 Stabilization of polycarbonates having high heat distortion temperatures Expired - Lifetime US5668204A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE4109810 1991-03-26
DE4109810.2 1991-06-07
DE4118705A DE4118705A1 (de) 1991-03-26 1991-06-07 Stabilisierung von hochwaermeformbestaendigem polycarbonat
DE4118705.9 1991-06-07

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US5668204A true US5668204A (en) 1997-09-16

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US (1) US5668204A (fr)
EP (1) EP0505869B1 (fr)
JP (1) JPH05112708A (fr)
DE (2) DE4118705A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6727303B2 (en) 2001-08-30 2004-04-27 Teijin Chemicals, Ltd. Flame retardant aromatic polycarbonate resin composition and molded articles thereof
US20070203275A1 (en) * 2004-03-16 2007-08-30 Sumitomo Chemical Company, Limited Organic Silicon-Based Compound And Method Of Producing The Same
US20120202034A1 (en) * 2011-02-03 2012-08-09 Jean-Francois Morizur Color and Heat Stable Polycarbonate Compositions and Methods of Making

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4122556C2 (de) * 1991-07-08 2002-11-28 Ticona Gmbh Mischungen aus thermoplastischen Polymeren und cyclischen Organosilikon-Verbindungen sowie die Verwendung der Mischungen
DE4213321A1 (de) * 1992-04-23 1993-10-28 Bayer Ag Thermostabilisierung von aromatischen Polycarbonaten
DE4224769C2 (de) * 1992-07-27 1994-11-10 Bayer Ag Verwendung von Siloxanen zur Veredelung von Polycarbonatabfällen
US5354796A (en) * 1992-10-01 1994-10-11 General Electric Company Low gloss thermoplastic molding compositions
DE4424105A1 (de) * 1994-07-08 1996-01-11 Bayer Ag Epoxigruppen enthaltende Siloxane und ihre Mischungen mit Polycarbonaten
DE4440684A1 (de) * 1994-11-15 1996-05-23 Bayer Ag Flammwidrige Polycarbonatformmassen
US5508344A (en) * 1994-11-22 1996-04-16 Bayer Corporation Low temperature drying of impact modified polycarbonate/polyester compositions
CA2161195A1 (fr) * 1994-11-22 1996-05-23 James P. Mason Melange de polycarbonate et de polyester resistant aux rayons gamma
US5556908A (en) * 1995-07-06 1996-09-17 Bayer Corporation Toughened thermoplastic molding composition
US5726236A (en) * 1995-07-06 1998-03-10 Bayer Corporation Impact modified thermoplastic molding composition
US5594059A (en) * 1995-07-06 1997-01-14 Bayer Corporation Impact modified thermoplastic molding composition containing polycarbonate and polyester
EP1426412A3 (fr) * 1995-07-06 2004-09-29 Bayer Corporation Composition thermoplastique de moulage résistante aux chocs à base de polycarbonate
US5728765A (en) * 1995-08-10 1998-03-17 Bayer Corporation Glass fiber-reinforced polycarbonate molding compositions having improved impact strenght

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US2999835A (en) * 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
GB1441367A (en) * 1973-05-26 1976-06-30 Bayer Ag Filled aromatic polycabonates with improved properties
US4130530A (en) * 1977-04-08 1978-12-19 General Electric Company Cyclic siloxane plasticized polycarbonate composition
US4147707A (en) * 1975-04-24 1979-04-03 Bayer Aktiengesellschaft Glass fiber-reinforced polycarbonates with improved mechanical properties containing 0.5 to 5.0% of organopolysiloxane
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US4221728A (en) * 1977-12-28 1980-09-09 General Electric Company Stabilized polycarbonate compositions
GB2057464A (en) * 1979-08-27 1981-04-01 Gen Electric Impact resistant polycarbonate compositions
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US4342681A (en) * 1979-05-21 1982-08-03 Bayer Aktiengesellschaft Use of organic silicon compounds in combination with oxetane compounds, dioxanes or tetrahydrofuranes for stabilizing and brightening polycarbonates which are free from phosphites and free from boric acid esters
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JPS62148560A (ja) * 1985-12-23 1987-07-02 Mitsubishi Chem Ind Ltd ポリカ−ボネ−ト樹脂組成物
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US2999835A (en) * 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
GB1441367A (en) * 1973-05-26 1976-06-30 Bayer Ag Filled aromatic polycabonates with improved properties
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US4197384A (en) * 1977-12-28 1980-04-08 General Electric Company Stabilized polycarbonate compositions
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JPS62148560A (ja) * 1985-12-23 1987-07-02 Mitsubishi Chem Ind Ltd ポリカ−ボネ−ト樹脂組成物
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US5100960A (en) * 1989-03-15 1992-03-31 Bayer Aktiengesellschaft Thermoplastic molding compositions of a polysiloxane block copolycarbonate and a polycarbonate based on certain dihydroxydiphenylcycloalkanes
US5025065A (en) * 1989-04-08 1991-06-18 Bayer Aktiengesellschaft Fire-retardant polycarbonates and polyesters
US5104945A (en) * 1989-04-21 1992-04-14 Bayer Aktiengesellschaft Heat resistant polycarbonate molding compositions
US5068302A (en) * 1989-08-15 1991-11-26 Bayer Aktiengesellschaft Polysiloxane-polycarbonate block copolymers based on certain dihydroxydiphenylcycloalkanes

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6727303B2 (en) 2001-08-30 2004-04-27 Teijin Chemicals, Ltd. Flame retardant aromatic polycarbonate resin composition and molded articles thereof
US20070203275A1 (en) * 2004-03-16 2007-08-30 Sumitomo Chemical Company, Limited Organic Silicon-Based Compound And Method Of Producing The Same
US7741393B2 (en) * 2004-03-16 2010-06-22 Sumitomo Chemical Company, Limited Organic silicon-based compound and method of producing the same
KR101127908B1 (ko) 2004-03-16 2012-03-21 스미또모 가가꾸 가부시끼가이샤 유기규소계 화합물 및 그 제조방법
US20120202034A1 (en) * 2011-02-03 2012-08-09 Jean-Francois Morizur Color and Heat Stable Polycarbonate Compositions and Methods of Making
US9234096B2 (en) * 2011-02-03 2016-01-12 Sabic Global Technologies B.V. Color and heat stable polycarbonate compositions and methods of making

Also Published As

Publication number Publication date
DE59208879D1 (de) 1997-10-16
DE4118705A1 (de) 1993-01-14
EP0505869A2 (fr) 1992-09-30
EP0505869A3 (en) 1992-12-30
JPH05112708A (ja) 1993-05-07
EP0505869B1 (fr) 1997-09-10

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